Nine N-aryl-2-chloronicotinamides: supramolecular structures in one, two and three dimensions

Structures are reported here for eight further substituted N-aryl-2-chloronicotinamides, 2-ClC5H3NCONHC6H4X-4'. When X = H, compound (I) (C12H9ClN2O), the molecules are linked into sheets by N-H (...) N, C-H (...) pi (pyridyl) and C-H (...) pi(arene) hydrogen bonds. For X = CH3, compound (II) (C13H11ClN2O, triclinic P (1) over bar with Z' = 2), the molecules are linked into sheets by N-H (...) O, C-H (...) O and C-H (...) pi (arene) hydrogen bonds. Compound (III), where X = F, crystallizes as a monohydrate ((C12H8ClFN2OH2O)-H-.) and sheets are formed by N-H (...) O, O-H (...) O and O-H (...) N hydrogen bonds and aromatic pi(...)pi stacking interactions. Crystals of compound (IV), where X = Cl (C12H8Cl2N2O, monoclinic P2(1) with Z' = 4) exhibit inversion twinning: the molecules are linked by N-H (...) O hydrogen bonds into four independent chains, linked in pairs by C-H (...) pi (arene) hydrogen bonds. When X = Br, compound (V) (C12H8BrClN2O), the molecules are linked into sheets by N-H (...) O and C-H (...) N hydrogen bonds, while in compound (VI), where X = I (C12H8ClIN2O), the molecules are linked into a three-dimensional framework by N-H (...) O and C-H (...) pi(arene) hydrogen bonds and an iodo (...) N(pyridyl) interaction. For X = CH3O, compound VII) (C13H8ClN3O, triclinic P (1) over bar with Z' = 2), where X =CN, forms a complex three-dimensional framework by N-H (...) N, C-H (...) N and C-H-... O hydogen bonds and two independant aromatic pi (...) pi stacking interactions.